In contrast to alternative measures to risk, value at risk VaR has important virtues - intelligibility, comparability, and practicality - that make it a potentially valuable tool for strategic decision making and capital management in a wide variety of industries. However, capital-management decisions in most industries - including financial services, such as property/casualty insurance - have time horizons far longer than the one day horizon that prevails in commercial and investment banking, where the use of VaR is now concentrated. For VaR to be usefully applied to long-horizon decisions, it must address three fundamental problems unique to that context: estimation risk, adaptive risk modification, and franchise risk. This paper describes each of these problems, shows how they can be solved, and provides examples applicable to property/casualty insurance.